Concise synthesis of the chemopreventitive agent (±)-deguelin via a key 6-endo hydroarylation

被引：53

作者：

Pastine, SJ ^{[1
]}

Sames, D ^{[1
]}

机构：

[1] Columbia Univ, Dept Chem, New York, NY 10027 USA

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 22期

关键词：

D O I：

10.1021/ol035419j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHIC] A concise total synthesis of (+/-)-deguelin was achieved with a longest linear sequence of six steps in 68% yield. A key step was the platinum-catalyzed 6-endo hydroarylation of an alkynone intermediate.

引用

页码：4053 / 4055

页数：3

共 18 条

[1] NOVEL AND EFFICIENT SYNTHESIS OF ROTENOIDS VIA INTRAMOLECULAR RADICAL ARYLATION [J].

AHMADJUNAN, SA ;

AMOS, PC ;

WHITING, DA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (05) :539-545

[2] ROTENOID INTERCONVERSION - SYNTHESIS OF DEGUELIN FROM ROTENONE [J].

ANZEVENO, PB .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (14) :2578-2580

[3] Ru(II)- and Pt(II)-catalyzed cycloisomerization of ω-aryl-1-alkynes.: Generation of carbocationic species from alkynes and transition metal halides and its interception by an aromatic ring [J].

Chatani, N ;

Inoue, H ;

Ikeda, T ;

Murai, S .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (16) :4913-4918

[4] Effects of deguelin on the phosphatidylinositol 3-kinase/Akt pathway and apoptosis in premalignant human bronchial epithelial cells [J].

Chun, KH ;

Kosmeder, JW ;

Sun, SH ;

Pezzuto, JM ;

Lotan, R ;

Hong, WK ;

Lee, HY .

JNCI-JOURNAL OF THE NATIONAL CANCER INSTITUTE, 2003, 95 (04) :291-302

[5] SYNTHETIC MODULATION OF THE PERIPHERAL 2-OXYGENATION, 3-OXYGENATION, 9-OXYGENATION AND 12-OXYGENATION PATTERN OF ROTENOIDS [J].

CROMBIE, L ;

JOSEPHS, JL .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (21) :2591-2597

[6] Anticancer action of cube insecticide:: Correlation for rotenoid constituents between inhibition of NADH:ubiquinone oxidoreductase and induced ornithine decarboxylase activities [J].

Fang, NB ;

Casida, JE .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1998, 95 (07) :3380-3384

[7] TOTAL SYNTHESIS OF DL-DEGUELIN (SYNTHESIS OF ROTENOIDS V) [J].

FUKAMI, H ;

ODA, J ;

NAKAJIMA, M ;

SAKATA, G .

AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1961, 25 (03) :252-&

[8] EXPEDIENT SYNTHESES OF THE ROTENOID AND THIOROTENOID SYSTEMS [J].

GABBUTT, CD ;

HEPWORTH, JD ;

HERON, BM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (06) :653-657

[9]

GENEIVE HE, 2001, TETRAHEDRON, V57, P5235

[10]

Gerhauser C, 1997, CANCER RES, V57, P3429

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